Trifluoroacetic acid → HCID 85189178, compound

HRID 1184297Notes

Reaction equation

HRID 1184297 reaction equation
C([O:5][C:6](=[O:24])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH:20]=[CH:21][CH2:22][Br:23])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:23][CH2:22][CH:21]=[CH:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:6]([OH:24])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53399024tert-Butyl 17-bromo-4,7,10,13-tetraoxaheptadec-15-en-1-oate

Product 1

HCID 85189178HCID 85189178, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At RT, a solution of 1 g of 3-(2-{2-[2-(4-bromo-but-2-enyloxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid tert-butyl ester (commercially available), 6 ml of TFA and 3 ml of DCM is stirred during 3 hrs, and then concentrated to dryness under RP. The oily residue is diluted with toluene and concentrated to dryness under RP affording 853 mg of 3-(2-{2-[2-(4-bromo-but-2-enyloxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid in the form of a brown oil.

Workup

  1. concentrationconcentrated to dryness under RP
  2. additionThe oily residue is diluted with toluene
  3. concentrationconcentrated to dryness under RP

Sources & evidence

ORD record
ord-e50903a50cdf4bbfb7f7e6ef1db14eda
Source dataset
uspto-grants-2014_03
Patent number
US08668910B2

Reaction notes

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